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I've looked at life from both sides now

From win and lose and still somehow

It's life's illusions I recall …

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Joni Mitchell was on the cusp when she wrote the song Both Sides, Now. She has described it as a meditation on reality and fantasy – "an idea that was so big it seemed like I'd just scratched the surface of it." She would continue to scratch. Though written by a young artist, it has the feel of deep retrospection, much like John Lennon's In My Life, a song that took on a different sort of poignancy when sung by a dying Johnny Cash in 2002.

Both Sides, Now was a hit for Judy Collins in 1967. Mitchell recorded it herself for 1969's Clouds, and again on the 2000 album Both Sides Now. The revisited version was done in a softly dramatic croon. Mitchell, her voice notched down to alto, was a different person – an interpreter, now, not a confessor, of her own words. The song – covered by everyone from Bing Crosby to Carly Rae Jepsen – was an instantaneous standard. But the writing was personal: a young star's growing realization that she was on the rise, that discovery lay ahead, and the recognition that much would be left behind. This kind of self-awareness is, of course, rare.

"Both Sides, Now is, at first, a meditation on clouds, the whimsical way a child sees them, as "ice-cream castles in the air," but there are two sides to everything, and as we mature, we stop seeing clouds for their simple beauty, but as a sign of rain or bad weather. It is like that with all things that seem at first so simple and beautiful, such as love and life. We start out with such natural optimism as children, and then as adults we tend to learn a bitter pessimism or brutal honesty, seeing clouds/life/love for what they are." – Catherine MacLellan, PEI singer-songwriter

Much like Neil Young's Sugar Mountain (which Mitchell answered with The Circle Game), Both Sides, Now ruminates on the subject of lost youth. Mitchell was born in 1943 in Fort Macleod, Alta., where she survived a bout of polio – as did Young, a younger victim of the same epidemic – to enjoy Lindy dancing and ukulele plucking. Later, she studied art in Calgary, but dropped out of school to embark on a folk-music career in Toronto.

The personal life of the then Joan Anderson was in much flux. She was pregnant by a fellow art student, and, as a single mother, placed her infant daughter in a foster home in early 1965. Shortly afterward she married her new musical partner, the American Chuck Mitchell. The baby was put up for adoption – mother and daughter reunited in 1997 – and the couple settled in Detroit.

The marriage was jive though. Soon, armed with a work visa and a new name (Joni), Mitchell was alone and on the rise in New York. Around that time, while on a plane, she was moved by the book she was reading – Saul Bellow's Henderson the Rain King – to look at the clouds below her. She immediately started writing Both Sides, Now.

In 1968, at the Philadelphia Folk Festival, Mitchell had what she called a "sensation." It was the dawning on her that she had had her head in the clouds long enough, and that her childhood preoccupations needed to be put aside. "There was a plummeting into the Earth, tinged with a little bit of apprehension and fear," she told Rolling Stone magazine years later. "Shortly after that, everything began to change."

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Some songs force themselves into existence, stories that cannot help but be told or vulnerabilities that insist on being confessed.

"Both Sides, Now is one of those songs. The phrases belong to the melody in such a precise and delicate way, one can only surrender to the celebration of human frailty. Where songwriting is at times a lonely and cerebral craft, I find the songs that seem to introduce themselves to even the writer are among the most valued and romantic of the art form. It is those elusive bits of beauty that keep us all searching." – Amelia Curran, Halifax-based singer-songwriter

Mitchell's work from 1969 to 1971 (covering the albums Clouds, Ladies of The Canyon and Blue) represented a bolder performer and songwriter. Her groundbreaking personal style of writing was a reaction to her growing fame. Uncomfortable that fans would worship her without knowing her, she gave them the full Joni.

The raw Joni was evident on The River, a crushing ballad of escape and deep regret: "I'm so hard to handle, I'm selfish and I'm sad, now I've gone and lost the best baby that I ever had." Some of Mitchell's peers found the material on Blue too close to the bone. Mitchell hid nothing, though, and the confessional singer-songwriter was born.

"Both Sides, Now is a vivid affirmation of Joni's identity as a painter and an idealist. Clouds are a favourite subject of landscape painters, and the images Joni describes embody their capricious nature. She first sees them with wonder and hope, and when they change shape, she begins to doubt her feelings. The idea of understanding something as mercurial as clouds, or love, or friendship seems an impossible task that would mean accepting change without feeling regret or disappointment. Her conclusion, "I really don't know life at all," is bittersweet and sincere, and appeals to anyone hurt by something that once brought them joy." – Molly Sweeney, Montreal singer-songwriter

After Blue, Mitchell took a break from the road for a while and returned to Canada. The nuanced work that followed – including the painterly classic Court and Spark from 1974 – was marked by topicality and jazzier directions, including a collaboration with that genre's dying double-bass great (on 1979's Mingus).

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By 2002, Mitchell had left the business, but she returned with her first collection of new songs in a decade for 2007's Shine.

Mitchell, retired from music, is alive and painting in Los Angeles.

It was At L.A.'s Troubadour, where she spoke a few years ago with English singer-songwriter James Blake about artistic longevity. On the flight back to London, Blake wrote Overgrown, with the line: "I don't want to be a star but a stone on the shore, a lone door frame in a war," inspired by Mitchell's durable relevance.

For Luminato, Mitchell will be interviewed onstage at Isabel Bader Theatre on Sunday. On Tuesday and Wednesday at Massey Hall, a collection of singers will interpret the inimitable singer-songwriter's material. The honouree herself will recite a new poem, with musical accompaniment. Does Mitchell, at 69, know life now? Who is to say? Her audience does know her, though, which is about all she could have ever asked for.

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